Gender discrimination and sexual harassment persist on college campuses across the United States. This seems especially obvious at the beginning of the academic year when many freshman women and their parents are welcomed to campus with sexually explicit signs displayed on all-male residences. But, sometimes, sexual harassment and gender discrimination takes a subtler form, creating unique challenges for administrators. This article presents the true case of a professional fraternity party gone awry, testing the leadership skills of several college administrators. The case provides a platform for educational leadership students to apply the theories they are learning in their preparation programs to real-life situations. This case is important and timely as educational leaders across the p-20 pipeline struggle to navigate the U.S. Department of Education Office for Civil Rights' 2011 directives concerning defining and responding to allegations of sexual assault and harassment.